U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H25N3S
Molecular Weight 339.498
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERAZINE

SMILES

CN1CCN(CCCN2C3=C(SC4=C2C=CC=C4)C=CC=C3)CC1

InChI

InChIKey=WEYVCQFUGFRXOM-UHFFFAOYSA-N
InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3

HIDE SMILES / InChI

Molecular Formula C20H25N3S
Molecular Weight 339.498
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12523495 and http://www.genome.jp/dbget-bin/www_bget?D01412

Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. Perazine is an older antipsychotic drug first introduced in the 1950s. It is suggested to have a low level of side effects (especially for movement disorders). Its use is regional and restricted to countries like Germany, Poland, the Netherlands and the former Yugoslavia. Perazine has being shown to be a potent inhibitor of human CYP1A2. It acts as a dopamine antagonist.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Cytochrome P450 2B, Rattus norvegicus
45.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Taxilan

Approved Use

Taxilan is used in the treatment of schizophrenia
PubMed

PubMed

TitleDatePubMed
[Electroconvulsive therapy in treatment of acute life threatening catatonia in toxic epidermal necrolysis (Lyell syndrome)].
1992 May
Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro.
2000 Sep
[Neuroleptic malignant syndrome--case report].
2001
The effect of selective serotonin reuptake inhibitors (SSRIs) on the pharmacokinetics and metabolism of perazine in the rat.
2001 Apr
Relevance of liver enzyme elevations with four different neuroleptics: a retrospective review of 7,263 treatment courses.
2001 Apr
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia].
2001 Jan-Feb
Neuroleptics normalize increased release of interleukin- 1 beta and tumor necrosis factor-alpha from monocytes in schizophrenia.
2001 Jul 1
Examination of iron (III) and hexacyanoferrate (III) ions as reagents for the spectrophotometric determination of promazine and perazine.
2001 Nov-Dec
Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver.
2001 Nov-Dec
Prevalence of obesity in adolescent and young adult patients with and without schizophrenia and in relationship to antipsychotic medication.
2001 Nov-Dec
Intracellular distribution of psychotropic drugs in the grey and white matter of the brain: the role of lysosomal trapping.
2001 Oct
[Therapy of subclinical (subdiagnostic) syndromes of schizophrenia spectrum].
2001 Sep
Perazine for schizophrenia.
2002
Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4.
2002 Jul-Aug
Switching to amisulpride due to hepatic complications.
2002 May
The contribution of cytochrome P-450 isoenzymes to the metabolism of phenothiazine neuroleptics.
2002 Oct
Schizophrenia.
2003 Dec
Antipsychotic efficacy of the antidepressant trimipramine: a randomized, double-blind comparison with the phenothiazine perazine.
2003 Mar-Apr
The AMUP study for drug surveillance in psychiatry - a summary of inpatient data.
2004 Mar
Acute psychosis with a mediastinal carcinoma metastasis.
2005 Jan
Increased serum interleukin-1beta and interleukin-6 in elderly, chronic schizophrenic patients on stable antipsychotic medication.
2005 Jun
Analysis of phenothiazines in human body fluids using disk solid-phase extraction and liquid chromatography.
2005 Nov-Dec
Interactions between neuroleptics and CYP2C6 in rat liver--in vitro and ex vivo study.
2005 Nov-Dec
Metabolic profiling of CSF: evidence that early intervention may impact on disease progression and outcome in schizophrenia.
2006 Aug
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Characterization of human cytochrome p450 enzymes involved in the metabolism of the piperidine-type phenothiazine neuroleptic thioridazine.
2006 Mar
Quantitative determination of forty-eight antidepressants and antipsychotics in human serum by HPLC tandem mass spectrometry: a multi-level, single-sample approach.
2006 Oct 20
[Ischemic colitis without atherosclerosis?].
2007 Mar 30
The activity of cytochrome P450 CYP2B in rat liver during neuroleptic treatment.
2007 Sep-Oct
Typical and atypical antipsychotics--the misleading dichotomy. Results from the Working Group 'Drugs in Psychiatry' (AGATE).
2008
The effect of antipsychotic medication on sexual function and serum prolactin levels in community-treated schizophrenic patients: results from the Schizophrenia Trial of Aripiprazole (STAR) study (NCT00237913).
2008 Dec 22
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.
2008 Feb
Amisulpride plus valproate vs haloperidol plus valproate in the treatment of acute mania of bipolar I patients: a multicenter, open-label, randomized, comparative trial.
2008 Jun
[Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples].
2008 Oct-Dec
Effects of typical and atypical antipsychotic drugs on gene expression profiles in the liver of schizophrenia subjects.
2009 Sep 16
Perazine at therapeutic drug concentrations inhibits human cytochrome P450 isoenzyme 1A2 (CYP1A2) and caffeine metabolism--an in vitro study.
2009 Sep-Oct
The role of CYP2D6 and TaqI A polymorphisms in malignant neuroleptic syndrome: two case reports with three episodes.
2010 Mar
Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines.
2010 Oct 15
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In acutely ill and severely disturbed patients 50 mg perazine at time-intervals of 30 minutes can be administered intramuscularly
The customary dose range recommended for this antipsychotic under in-patient conditions is 75-600 mg/day (maximum 1000 mg/day).
Route of Administration: Oral
In Vitro Use Guide
About 80% of basal human CYP1A2 activity was reduced by the therapeutic concentrations of perazine (5-10 uM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:18:23 UTC 2023
Edited
by admin
on Fri Dec 15 16:18:23 UTC 2023
Record UNII
8915147A2B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERAZINE
MI   WHO-DD  
Common Name English
PROCHLORPERAZINE MALEATE IMPURITY B [EP IMPURITY]
Common Name English
10-(3-(4-METHYLPIPERAZIN-1-YL)PROPYL)PHENOTHIAZINE
Systematic Name English
PERAZINE [MI]
Common Name English
Perazine [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QN05AB10
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
WHO-ATC N05AB10
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
NCI_THESAURUS C66883
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
Code System Code Type Description
RXCUI
8042
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY RxNorm
CAS
84-97-9
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
WIKIPEDIA
Perazine
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
NCI_THESAURUS
C81093
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
FDA UNII
8915147A2B
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
SMS_ID
100000079987
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
DRUG CENTRAL
2100
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
PUBCHEM
4744
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID6048628
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
DRUG BANK
DB12710
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL1697766
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
MESH
D010464
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
EVMPD
SUB14811MIG
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
MERCK INDEX
m8535
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
201-578-9
Created by admin on Fri Dec 15 16:18:23 UTC 2023 , Edited by admin on Fri Dec 15 16:18:23 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY